Abstract
BackgroundThe benzhydryl ether moiety is widely distributed in nature and constitutes a key structural motif in numerous molecules of significant biological potential and of prospective clinical uses. Solvent-free and cost-effective facile synthesis of symmetrical bis(benzhydryl)ethers is, thus, much desirable.ResultsA simple and efficient method for the facile synthesis of symmetrical bis(benzhydryl)ethers directly from the corresponding benzhydrols has been developed using a catalytic amount of p-toluenesulfonyl chloride (5 mol%) at an oil bath temperature of 110°C under solvent-free conditions.ConclusionsOperational simplicity, low reagent loading, high product yields, short reaction time, and solvent-free conditions are the notable advantages of the present method.
Highlights
The benzhydryl ether moiety is widely distributed in nature and constitutes a key structural motif in numerous molecules of significant biological potential and of prospective clinical uses
The benzhydryl ether moiety is abundant in a number of naturally occurring and biologically active compounds as well as molecules of potential clinical uses [1,2,3,4,5,6,7,8]; this motif was found as a partial structure in a few new chemical entities showing therapeutic activity as well [9]
In continuation of our effort to develop green and solvent-free synthetic methodologies for organic transformations [22,23,24,25,26,27,28], we wish to report in this communication a convenient and straightforward protocol for the efficient synthesis of symmetrical bis(benzhydryl)ethers in excellent yields using a catalytic amount of p-toluenesulfonyl chloride under solvent-free conditions (Scheme 1)
Summary
The benzhydryl ether moiety is widely distributed in nature and constitutes a key structural motif in numerous molecules of significant biological potential and of prospective clinical uses. Results: A simple and efficient method for the facile synthesis of symmetrical bis(benzhydryl)ethers directly from the corresponding benzhydrols has been developed using a catalytic amount of p-toluenesulfonyl chloride (5 mol%) at an oil bath temperature of 110°C under solvent-free conditions. In continuation of our effort to develop green and solvent-free synthetic methodologies for organic transformations [22,23,24,25,26,27,28], we wish to report in this communication a convenient and straightforward protocol for the efficient synthesis of symmetrical bis(benzhydryl)ethers in excellent yields using a catalytic amount of p-toluenesulfonyl chloride under solvent-free conditions (Scheme 1). The process is very simple, cost-effective, and environmentally benign
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